A letter from Eryk Pruitt
Hillsborough for the Holidays: Shop, Dine, and Stay for the Show
Don’t go home after dinner — Hillsborough nightlife is brimming with music, storytelling, cocktails, and cheer all December long.
Every December, Hillsborough wraps itself in holiday charm. From the towering tree on Churton Street to the gingerbread displays in downtown shop windows, the town feels like something out of a snow globe. Visitors come for the gallery strolls, the gift shopping, and the warm dinners with family and out-of-town guests.
But here’s a little secret: when the plates are cleared and the boutiques flip their signs to CLOSED, the evening is just getting started.
Whether you’re full from crab cakes at Saratoga Grill or loaded down with shopping bags from Reinvintaged or Dwell, don’t drive home just yet. December’s calendar is packed with reasons to stick around. Live music, holiday trivia, script readings, and cozy cocktail specials give you every excuse to make Hillsborough’s nightlife part of your holiday tradition.
Stories, Song, and Seasonal Sass at Yonder
Hillsborough’s signature cocktail lounge and creative hub, Yonder, has a whole stocking’s worth of holiday entertainment lined up. Alongside regular jazz nights, open mics, and live music every weekend, you’ll find:
- Dec 3: Yonder Live Reels – “How the Grinch Stole Christmas”
A dramatic script reading of the holiday classic, complete with wild costumes, zany props, and just the right amount of Seussian mischief. - Dec 11: Noir at the Bar – Holiday Edition
Local authors—including Jill McCorkle, Eryk Pruitt, Richard Dansky, Meagan Lucas, and more—read holiday-themed crime stories that are equal parts festive and twisted. It’s perfectly paired with a spiked eggnog or a steaming hot buttered rum. - Dec 19: The Whiskey Honeys – Live Holiday Set
A local favorite returns to the stage with lush harmonies, vintage country soul, and a sleigh-full of seasonal tunes. Order a signature cocktail, sing along, and hit the dance floor with a room full of friends.
“Yonder makes every night feel like a curated holiday mixtape,” says Paige McNeal, Yonder’s bar manager. “It’s perfect for everyone, no matter if they find themselves on the naughty list or the nice list.”
Naughty or nice, make your holidays bright with festive events and spirits at Yonder Southern Cocktails and Wine.
Raise a Pint and Your Voice at Nash Street Tavern
Looking for holiday cheer with a little more flannel and a little less fuss? Cross the train tracks into West Hillsborough and settle into Nash Street Tavern, where the soundtrack is stomping and the pints are always cold.
- Dec 12: Deelin Ded’s Very Merry Jerry Xmas Holiday Jam
A psychedelic tribute to Jerry Garcia and the Grateful Dead with laid-back vibes and high-energy jams. Tie-dye is optional, but dancing is highly encouraged. - Dec 21: Beer & Hymns – Holiday Edition
This crowd-favorite singalong turns familiar carols into barroom ballads. Grab a beer, find a lyric sheet, and raise your voice with a room full of new friends. You may come for “Silent Night,” but you’ll stay for the harmony and hilarity. - Neighbors Helping Neighbors
“We are a donation center for Eno House Food Bank,” says Nash Street’s bar manager, Drew Bryant. “We have an active drive that will continue through Christmas, regardless of any governmental shutdowns.”
Nash Street keeps it real, keeps it loud, and keeps it local.
Friendly faces and cozy vibes abound at Nash Street Tavern, especially during the holidays.
Trivia, Sweaters, and Craft Cocktails at The Rookery
The Rookery might be the new kid on the block, but they’ve made a name for themselves as a go-to for cozy chaos and family fun during the holidays. This December, it’s offering a full slate of festive cheer:
- 12 Days of Cocktails
A rotating menu of seasonal drink specials—expect peppermint martinis, rosemary-spiked spritzes, and playful takes on holiday classics. - Wednesdays: Get Carded – Holiday Trivia Nights
In collaboration with the Orange County Public Library, these trivia nights test your knowledge of everything from reindeer names to Hallmark movie plots. Great for families, friends, and friendly rivalries. - Ugly Sweater Holiday Party (Date TBA)
Throw on the worst thing in your closet, grab a cocktail, and lean into the fun. Remember: the worse your sweater, the better your night.
The Rookery’s energy is festive, casual, and welcoming, much like Hillsborough itself.
Escape the cold with tropical vibes and fun times at The Rookery.
Make a New Holiday Tradition
While beloved holiday traditions like the Light Up the Night Holiday Parade on December 7th and the Solstice Lantern Walk on December 20 return this year, there’s no better time to discover everything else Hillsborough has to offer. After a long day of shopping, prop up your feet with a warm beverage.
Warm up at a local establishment after the Light Up the Night Holiday Parade.
Before the lanterns begin their journey, stop by Eno River Brewing. Their fire pits will be crackling and their seasonal brews flowing, with an open-air space where the kids can shake off all that cookie energy. It’s a perfect pre-walk stop, and the beginning of a longer night.
Eno River Brewing Company is the perfect stop for a locally brewed beverage.
After the parade, warm up with a hot toddy at Yonder, just around the corner on King Street. With its low lighting and deep couches, the chill of the season will melt away the moment you step inside.
One of the best things about Hillsborough nightlife? It’s easy. No cover charges. No reservations. No pretension. Just live music, great storytelling, seasonal drinks, and good company.
Whether you want to catch a reading, belt out a carol, win a round of trivia, or warm your hands beside a fire pit, there’s a spot waiting for you and it’s just around the corner from where you parked.
So, this December, shop local, dine well, and stick around for the show.
The night is young—and Hillsborough is just getting started.
(Photos by Alexandrea Lassiter, Amanda Boyd, Eryk Pruitt, and Jada Jarillo)
View festive gingerbread houses honoring local landmarks as you explore downtown Hillsborough.
“Hillsborough After Dark” is a series sponsored by Visit Hillsborough and highlighting some of the best our town on the Eno has to offer! Hillsborough has charm, history and — if you know where to look — some spectacular spots to visit After Dark! Check back to see what else Hillsborough has to offer, and for more local essays guiding your explorations and outings!
